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Worst Sexual Experience

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I feel sorry for all these small penis guys y'all have come across. Must suck for them not having much to work with.
 
okay, I got one.
it was my first time hooking up with a younger guy. we are pretty drunk after a brand new concert and decided to head back to his place to smoke and chill for a bit. well, when we get there we lay in his bed and start fooling around, so I ask if he has a condom. he gets up and starts rummaging through a drawer and says to me, "I'm really self conscious about my penis. it's small and slightly curved." I just roll my eyes, thinking 'wtf, shut up, and just grab a condom.' well, he finally tracks one down and joins me back in the bed. he, then, begins to sex me missionary; I could hardly feel him and he was seriously just flopping around like a fish. I suggested I get on top, you know, to make the situation at least a bit enjoyable. he then puts his finger to my mouth and tells me to "shhhh." he continues just flopping. so, I say one more time "here, let me get on top, though." he, again, puts his finger to my mouth and tells me to "shhhh." he then says, "I don't like when a girl is on top, I've heard of friends breaking their dicks and I never want that to happen to me" and just continues flopping. finally, after about, four minutes he cums. thank you lord. he then pulls out, but forgets/doesn't know, I have no idea how he missed the memo, but withdraws without holding the base of the condom and it is left stuck to the insides of my legs. I freak out saying "get this the fuck off me." I quickly removed the used rubber and throw it his direction. completely disappointed and grossed out, I left to the beautiful solitude of my house, where I proceeded to have awesome orgasms with my hitachi. seriously, WORSE SEX EVER! I call him fishboy now, when referring to him with friends.

it was that awkward sex, that virgins have in movies, the kind of sex you thought only existed in movies for comedic value. no, that really happens. and it was neither of our first times.
this is the perfect gif to demonstrate this four mins of my life.
8s9GRP9.gif
 
This one is pretty embarrassing on my part, I was only 18 and VERY naive.
The sex itself wasn't necessarily bad but it was an experience that made me realize I was a fucking idiot and was a turning point in my life.

After I graduated High School I started talking to this dude on Facebook from New Jersey who was a few years older than me. He was like 21 or 22 I think. I cannot remember how we met because we had zero mutual friends. Red flag #1.
I was extremely naive and thought we had a connection because we "talked" on the phone sometimes late at night. I put "talked" in quotation marks because we never really talked about anything. He just kinda made fun of me for everything and we had little to nothing in common. Red flag #2.

Turns out he was going on this road trip across the country with his dad for business and was staying the night in a town one state over. We discussed meeting because I figured this was the only chance I'd ever get to see him. I drove out that night by myself, VERY late, and the drive was about 2 1/2 hours. I finally arrived at this truck stop and we walked around talking for a little bit. He was kinda gross and had obviously been on the road for a really long time. We still had nothing in common and FOR SOME REASON I was like "yeah okay no problems here!"

We ended up going back to my car and having sex. I was on top of him while he sat in the passenger seat. I was on birth control so I was like "WE DON'T NEED A CONDOM LOL!", of course I felt like a badass being the chick who doesn't use condoms but now I realize I was just being super trashy. The sex was really rough and I remember him putting a finger in my ass even though I initially told him I was unsure about it (I had never had anything there before). I was marked up really bad with black/yellow bruises from spanks and bleeding rugburn on my knees, feet, and elbows.

I didn't get home until about 6:00 in the morning and felt completely disgusting. It was a humid summer night and I was sticky, sweaty, covered in spit and god knows what else. It took many years of experience, therapy, and working in the adult industry to teach me how DANGEROUS what I did was and how I'm lucky that consensual bruises and scrapes were the worst I got. I could have gotten kidnapped or raped or killed or something. :?

I still think about that night sometimes and just feel so dirty. How could I have been such an idiot? I was so excited about sleeping with a slightly older guy for the bragging rights I guess. :woops:
 
Can I just add another bad experience that will make some of you guys feel better?

It was a guy I was in a long distance relationship with and he wasn't experienced....He also had a curvature in his penis that pointed....down. Meaning the only way we could actually have sex was doggy.

When we did have sex, I ended up being in doggy while he grunted and groaned and I just...played FF7 while he was fucking me. I feel so bad now.
 
LilLitaRose said:
Can I just add another bad experience that will make some of you guys feel better?

It was a guy I was in a long distance relationship with and he wasn't experienced....He also had a curvature in his penis that pointed....down. Meaning the only way we could actually have sex was doggy.

When we did have sex, I ended up being in doggy while he grunted and groaned and I just...played FF7 while he was fucking me. I feel so bad now.

That might be my favorite story on this post so far.
 
I was seeing this guy (who in hindsight I think was married). I was 19, he was 31. He was absolutely gorgeous though, he was like a cross of sterophonics singer and colin farrell. He invited me round to his flat and we were watching a movie. It was ridiculously boring, I can't even remember what it was so I just got on top of him and started making out. He led me to a bedroom that was completely empty bar a bed, no pictures, no lamps, no nothing. He took his pants off and got grumpy I wouldn't let him do it without a condom (wasn't on any birth control at the time). He had the weirdest shaped penis, it was like a C and it hurt like fuck. I had to stay on top because he was so useless and it was painful in every other position. He came within minutes and I promptly dressed and left his house as quick as possible. He called a couple of times but I was mean and ignored them.

The other guy was a guy who's virginity I took. He literally had a penis that looked like this.

There was so much skin at the end and it was the tiniest thing in the world hard. Like the size of my little finger. Bless the poor little dude. Apparently he's gay now.
 

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Not exactly a sexual experience gone wrong. What happens with sex is what happens and I'm lucky... I don't tend to have bad sex. But this takes the cake for me.

I met this guy on the train one evening and it was great. He seemed super interesting, intelligent. I was a little younger and so I was easily enamored and not nearly so confident as I am now. So when he asked if I was doing anything that night you can be sure I had no plans.

We had a really great conversation and I was flirting heavily. Thoroughly expected to have the most awesome sex with him but I mentioned that I was having fun but we wouldn't have sex tonight because that's not how I roll, and he got a bit of a tweak in his hat. (warning sign)

So we end the date at his place and I tell him we can totally get to some cuddles and kissing and touching. And its really hot and heavy and I'm excited. All the way through this we've been talking about sexual experiences and he's telling me he's had sex with three hundred people and whatever.

I'm really turned on and ask him if he has any condoms. And he looks at me and goes:

"What? You want a condom? Only dirty people wear condoms."



What you say?

He really pressured me to have sex with him without a condom once I'd asked for one and was really surprised to find that I'm a viciously intelligent lady who drew the line at "I've had sex with three hundred people and never wear condoms and don't get STD tests... let me stick it in you!"... and I left as soon as the first bus ran with my contacts in a piece of cling wrap.
 
I might be going through my worst sexual experience at this time

I have a health condition where i fatigue easily; a problem that is increasingly prevalent as i get older (i’m only in my early 30s). I can’t even jog for a minute without feeling like i’m ready to black out. So months ago,i was trying to do the deed with a woman, but it was like working up a steep incline when trying to please her while being pleased. I simply couldn’t go without feeling like my energy was already spent. That experience, coupled with a bit of social anxiety, left me beyond embarrassed that i can’t help but feel sorta scared when thinking about touching another woman, which only adds to my embarrassment. Also, i'm not one of those people who can get action on tap with relative ease, so imagine how fuckin frustrating this is.

I’ve been working a lot on my health, particularly the last few months. There are days where it takes a toll on my daily life to the point where i can’t seem to function properly, which leaves me fuckin irritable. It’s one of those things i hafta live with. As far as that traumatic sexual experience is concerned, i’m slowly coming to terms with it, by reminding myself it is what it is.
 
mutantdonut said:
I might be going through my worst sexual experience at this time

I have a health condition where i fatigue easily; a problem that is increasingly prevalent as i get older (i’m only in my early 30s). I can’t even jog for a minute without feeling like i’m ready to black out. So months ago,i was trying to do the deed with a woman, but it was like working up a steep incline when trying to please her while being pleased. I simply couldn’t go without feeling like my energy was already spent. That experience, coupled with a bit of social anxiety, left me beyond embarrassed that i can’t help but feel sorta scared when thinking about touching another woman, which only adds to my embarrassment. Also, i'm not one of those people who can get action on tap with relative ease, so imagine how fuckin frustrating this is.

I’ve been working a lot on my health, particularly the last few months. There are days where it takes a toll on my daily life to the point where i can’t seem to function properly, which leaves me fuckin irritable. It’s one of those things i hafta live with. As far as that traumatic sexual experience is concerned, i’m slowly coming to terms with it, by reminding myself it is what it is.

I can very much relate to easily fatigued due to health reasons. And I'm sorry you are going through that pain. Hope things get better, and just know that, it's not something to be ashamed of. Like you said, it's something you have to live with.
You are so nice on here, and you shouldn't feel any less. :<
 
ok not worst but kinda silly. i was in a ldr, didn't have any toys and my boyfriend wanted to see something other than fingers inside me while we were gettin down on skype. i was cool with the idea, washed some random objects like pens, hairbrush end etc etc, but then he saw my stash of candy and told me to put a fundip stick up my vagine. :cool: pretty young so i was like hell yea! then proceeded to lose grasp of it within 5 seconds and spent 5 minutes trying to get it out. he said it was hot, and that whole month i was really paranoid about getting a yeast infection after i googled "sugar vagina" the next day haha
 
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